JP5975870B2 - Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode - Google Patents
Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode Download PDFInfo
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- JP5975870B2 JP5975870B2 JP2012517399A JP2012517399A JP5975870B2 JP 5975870 B2 JP5975870 B2 JP 5975870B2 JP 2012517399 A JP2012517399 A JP 2012517399A JP 2012517399 A JP2012517399 A JP 2012517399A JP 5975870 B2 JP5975870 B2 JP 5975870B2
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- 230000005693 optoelectronics Effects 0.000 title claims 10
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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Description
本記載は、有機光電子素子用化合物、それを含む有機発光ダイオード、および前記有機発光ダイオードを含む表示装置に関する。 This description is an organic photoelectric child element compound, an organic light emitting diode containing the same, and a display device including the organic light emitting diode.
光電子素子(optoelectric device)は広い意味で光エネルギーを電気エネルギーに変換したり、電気エネルギーを光エネルギーに変換する素子である。前記光電子素子は、有機発光ダイオード(OLED:Organic‐Light Emitting Diodes)、太陽電池、トランジスタなどを例に挙げられる。特に、有機発光ダイオードは、近年、平板ディスプレイ(flat panel display)の需要が増加することに伴って注目されている。 Photoelectron element (opto electric device) is to convert light energy into electrical energy in a broad sense, it is a device that converts electrical energy into light energy. The photoelectron device, an organic light emitting diode (OLED: Organic-Light Emitting Diodes ), solar cells, and as an example, such as a transistor. In particular, organic light emitting diodes have attracted attention in recent years as demand for flat panel displays increases.
有機発光ダイオードに電流を加えると、陽極と陰極からそれぞれ正孔と電子が注入され、注入された正孔と電子はそれぞれの正孔輸送層(HTL)と電子輸送層(ETL)へ移動し発光層で再結合して発光励起子を形成する。このように形成された発光励起子は基底状態に遷移しながら光を放出する。前記光は発光メカニズムにより一重項励起子を利用する蛍光と三重項励起子を利用する燐光とに分けられ、前記蛍光および燐光は有機発光ダイオードの発光源として使用され得る(D.F.O’Brien,Appl.Phys.Lett.,74(3),442、1999;M.A.Baldo,Appl.Phys.lett.,75(1),4、1999)。 When an electric current is applied to the organic light emitting diode, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons move to the respective hole transport layer (HTL) and electron transport layer (ETL) to emit light. Recombination in the layers forms luminescent excitons. The luminescence excitons thus formed emit light while transitioning to the ground state. The light is divided into fluorescence using singlet excitons and phosphorescence using triplet excitons according to an emission mechanism, and the fluorescence and phosphorescence can be used as a light emitting source of an organic light emitting diode (DFO '). Brien, Appl. Phys. Lett., 74 (3), 442, 1999; MA Baldo, Appl. Phys. Lett., 75 (1), 4, 1999).
電子が基底状態から励起状態に遷移すると、項間交差(intersystem crossing)を通じて一重項励起子が三重項励起子に非発光遷移され、前記三重項励起子は再び基底状態に遷移して光を放出する。この時の発光を燐光発光という。前記三重項励起子は基底状態に直接遷移することはできず、必ず電子スピンのフリッピング段階を経なければならない。したがって、燐光発光は蛍光発光よりも半減期(発光時間、寿命)が長いという特性を有する。 When an electron transitions from a ground state to an excited state, a singlet exciton is non-radiatively transferred to a triplet exciton through intersystem crossing, and the triplet exciton again transitions to a ground state to emit light. To do. The light emission at this time is called phosphorescence light emission. The triplet exciton cannot make a direct transition to the ground state, and must pass through an electron spin flipping step. Therefore, phosphorescence has a characteristic that it has a longer half-life (emission time, lifetime) than fluorescence.
また、正孔と電子が再結合して発光励起子を形成する場合、三重項励起子は一重項励起子よりも約3倍多く生成される。蛍光物質は、一重項励起状態を25%有し発光効率に限界がある。しかし、燐光は三重項励起子の発生確率75%、および一重項励起状態である25%まで使用することができて、理論的な内部量子効率は100%となる。つまり、燐光発光物質は蛍光発光物質に比べて約4倍大きな発光効率を達成することができるという長所がある。 When holes and electrons are recombined to form luminescent excitons, triplet excitons are generated about three times as many as singlet excitons. The fluorescent material has a singlet excited state of 25% and has a limited light emission efficiency. However, phosphorescence can be used up to a generation probability of triplet excitons of 75% and a singlet excited state of 25%, and the theoretical internal quantum efficiency is 100%. That is, the phosphorescent material has an advantage that it can achieve luminous efficiency about four times larger than that of the fluorescent material.
一方、有機発光ダイオードの効率と安定性を増加させるために発光層にホスト物質とドーパントを共に添加することができる。前記ホスト物質としては、4,4’−N,N’−ジカルバゾールビフェニル(CBP)が主に使用されていた。しかし、CBPは構造的対称性が非常に高いため、結晶化し易く、熱的安定性が低いため、素子の耐熱試験中に、短絡や画素欠陥が発生する短所があった。また、CBPのような大部分のホスト物質は正孔の移動速度が電子の移動速度よりも速いため、発光層で励起子が効率的に形成され、素子の発光効率が減少する短所があった。 Meanwhile, both a host material and a dopant can be added to the light emitting layer to increase the efficiency and stability of the organic light emitting diode. As the host material, 4,4'-N, N'-dicarbazole biphenyl (CBP) was mainly used. However, since CBP has very high structural symmetry, it is easy to crystallize and has low thermal stability. Therefore, short circuit and pixel defects occur during the heat resistance test of the device. In addition, since most host materials such as CBP have a hole moving speed higher than an electron moving speed, excitons are efficiently formed in the light emitting layer, and the light emitting efficiency of the device is reduced. .
また、低分子ホスト物質は、一般に真空蒸着法を用いるため、湿式工程に比べて製造コストが高いという短所があった。また、大部分の低分子ホスト物質は有機溶媒に対する溶解度が低いため、湿式工程に適用できず優れた膜特性を有する有機薄膜層を形成できなかった。 In addition, since the low molecular weight host material generally uses a vacuum deposition method, it has a disadvantage in that the manufacturing cost is higher than that of a wet process. In addition, since most low-molecular host materials have low solubility in organic solvents, they cannot be applied to the wet process and an organic thin film layer having excellent film characteristics cannot be formed.
したがって、効率および寿命に優れた有機光電子素子を実現するためには、電気的、熱的安定性に優れ、正孔と電子を全て良好に伝達することができるバイポーラ特性を有する燐光のホスト物質および電荷輸送物質を開発し、正孔や電子を良好に伝達することができる物質を混合して使用することができるホスト物質の開発が必要である。 Therefore, in order to realize an excellent organic light electronic device efficiency and lifetime, electrical, excellent thermal stability, phosphorescent host material having a bipolar property of holes and electrons can be all transmitted well In addition, it is necessary to develop a charge transport material and to develop a host material that can be used by mixing a material that can transmit holes and electrons well.
本発明の一実施形態は、熱的安定性に優れ、正孔と電子を全て良好に伝達することができる有機光電子素子用化合物を提供する。 An embodiment of the present invention is excellent in thermal stability, to provide an organic photoelectric child element compound for all holes and electrons can be transmitted well.
本発明の他の実施形態は、前記有機光電子素子用化合物を含む効率および駆動電圧特性に優れた有機発光ダイオードを提供する。 Another embodiment of the present invention provides an organic light emitting diode with excellent efficiency and the driving voltage characteristic including the organic photoelectric child element compound.
本発明のさらなる他の実施形態は、前記有機発光ダイオードを含む表示装置を提供する。 Still another embodiment of the present invention provides a display device including the organic light emitting diode .
本発明の一実施形態によれば、下記の化学式1および化学式2で表される置換基を有する有機光電子素子用化合物が提供される。 According to an embodiment of the present invention, an organic photoelectric child element compound having a substituent represented by Formulas 1 and 2 below are provided.
前記化学式1および2において、
Lは、2価〜7価の連結基であって、オキシド基、アミン基、ホスホニル基、ホスホネート基、スルホニル基、スルホネート基、置換されたまたは非置換のC1〜C30のアルキレン基、置換されたまたは非置換のC1〜C30のヘテロアルキレン基、置換されたまたは非置換のC3〜C30のシクロアルキレン基、置換されたまたは非置換のC1〜C30のヘテロシクロアルキレン基、置換されたまたは非置換のC6〜C30のアリーレン基、置換されたまたは非置換のC2〜C30のヘテロアリーレン基またはこれらの組み合わせであり、
R1 およびR 2 は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、置換されたまたは非置換のC6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせであり、
R 3 〜R 5 は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせであり、
aは、2〜5の整数である。
In Formulas 1 and 2,
L is a divalent to 7-valent linking group, and is an oxide group, amine group, phosphonyl group, phosphonate group, sulfonyl group, sulfonate group, substituted or unsubstituted C1-C30 alkylene group, substituted Or an unsubstituted C1-C30 heteroalkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted A C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof,
R 1 and R 2 are the same or different from each other, and each independently represents hydrogen, a carbazolyl group, a C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, C2-C30 A heteroaryl group, a C6-C30 arylamine group, or a combination thereof,
R 3 to R 5 are the same as or different from each other, and each independently represents hydrogen, a carbazolyl group, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C6- An arylamine group of C30 or a combination thereof,
a is an integer of 2-5.
特に、前記R1およびR2は、互いに同一または異なるものであって、それぞれ独立して、カルバゾリル基、C1〜C30のアルキル基、置換されたまたは非置換のC6〜C30のアリール基、C2〜C30のヘテロアリール基またはこれらの組み合わせであり、R3〜R5は、互いに同一または異なるものであって、それぞれ独立して、水素、C1〜C30のアルキル基、C6〜C30のアリール基またはこれらの組み合わせであってもよい。 In particular, R 1 and R 2 may be the same or different from each other, and each independently represents a carbazolyl group, a C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, C2- A heteroaryl group of C30 or a combination thereof, and R 3 to R 5 are the same or different from each other, and each independently represents hydrogen, a C1-C30 alkyl group, a C6-C30 aryl group, or these A combination of these may be used.
前記化学式1は、下記の化学式1aで表されうる。 The chemical formula 1 may be represented by the following chemical formula 1a.
前記化学式1aにおいて、
Ra1およびRa2は、互いに同一または異なるものであって、それぞれ独立して、水素またはC1〜C10のアルキル基であり、
R3は、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせである。
In Formula 1a,
Ra 1 and Ra 2 are the same or different from each other, and each independently represents hydrogen or a C1-C10 alkyl group,
R 3 is hydrogen, a carbazolyl group, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C6-C30 arylamine group, or a combination thereof.
また、前記化学式2は、下記の化学式2a〜2cのいずれかで表されうる。 The chemical formula 2 may be represented by any of the following chemical formulas 2a to 2c.
前記化学式2a〜2cにおいて、
Lは、2価〜7価の連結基であって、オキシド基、アミン基、ホスホニル基、ホスホネート基、スルホニル基、スルホネート基、置換されたまたは非置換のC1〜C30のアルキレン基、置換されたまたは非置換のC1〜C30のヘテロアルキレン基、置換されたまたは非置換のC3〜C30のシクロアルキレン基、置換されたまたは非置換のC1〜C30のヘテロシクロアルキレン基、置換されたまたは非置換のC6〜C30のアリーレン基、置換されたまたは非置換のC2〜C30のヘテロアリーレン基またはこれらの組み合わせであり、
R4およびR5は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせであり、
aは、2〜5の整数である。
In the chemical formulas 2a to 2c,
L is a divalent to 7-valent linking group, and is an oxide group, amine group, phosphonyl group, phosphonate group, sulfonyl group, sulfonate group, substituted or unsubstituted C1-C30 alkylene group, substituted Or an unsubstituted C1-C30 heteroalkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted A C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof,
R 4 and R 5 are the same or different from each other, and are independently hydrogen, carbazolyl group, C1-C30 alkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, C6- An arylamine group of C30 or a combination thereof,
a is an integer of 2-5.
また、前記化学式2のLは、下記の化学式2d〜2jまたはこれらの組み合わせで表される化合物から誘導された2価〜7価の連結基でありうる。 In addition, L in Chemical Formula 2 may be a divalent to 7-valent linking group derived from a compound represented by the following Chemical Formulas 2d to 2j or a combination thereof.
前記化学式2d〜2jにおいて、
Q1〜Q6は、互いに同一または異なるものであって、それぞれ独立して、置換されたまたは非置換のN原子、置換されたまたは非置換のP原子、置換されたまたは非置換のS原子、置換されたまたは非置換のO原子、置換されたまたは非置換のC原子またはこれらの組み合わせであり、この時、前記「置換された」とは、水素、オキシド基、シアノ基、ハロゲン基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基またはこれらの組み合わせで置換されたものを意味する。
In the chemical formulas 2d to 2j,
Q 1 to Q 6 are the same or different from each other, and each independently represents a substituted or unsubstituted N atom, a substituted or unsubstituted P atom, or a substituted or unsubstituted S atom. A substituted or unsubstituted O atom, a substituted or unsubstituted C atom, or a combination thereof, wherein the “substituted” means hydrogen, an oxide group, a cyano group, a halogen group, A C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group or a combination thereof is meant.
前記化学式2において、aは、2または3でありうる。 In Formula 2, a may be 2 or 3.
前記化学式2のLは、下記の化学式2kで表されうる。 L in Formula 2 may be represented by the following Formula 2k.
また、前記有機光電子素子用化合物は、下記の化学式3〜化学式8で表されうる。 Moreover, the organic photoelectric child element compound may be represented by Chemical Formula 3 to Formula 8 below.
前記化学式3〜8において、
Lは、2価〜7価の連結基であって、オキシド基、アミン基、ホスホニル基、ホスホネート基、スルホニル基、スルホネート基、置換されたまたは非置換のC1〜C30のアルキレン基、置換されたまたは非置換のC1〜C30のヘテロアルキレン基、置換されたまたは非置換のC3〜C30のシクロアルキレン基、置換されたまたは非置換のC1〜C30のヘテロシクロアルキレン基、置換されたまたは非置換のC6〜C30のアリーレン基、置換されたまたは非置換のC2〜C30のヘテロアリーレン基またはこれらの組み合わせであり、
R1〜R10は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせである。
In the chemical formulas 3 to 8,
L is a divalent to 7-valent linking group, and is an oxide group, amine group, phosphonyl group, phosphonate group, sulfonyl group, sulfonate group, substituted or unsubstituted C1-C30 alkylene group, substituted Or an unsubstituted C1-C30 heteroalkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted A C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof,
R 1 to R 10 are the same as or different from each other, and each independently represents hydrogen, a carbazolyl group, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C6- A C30 arylamine group or a combination thereof.
また、前記有機光電子素子用化合物は、下記の化学式9〜化学式33で表されうる。 Moreover, the organic photoelectric child element compound may be represented by Chemical Formula 9 to Formula 33 below.
前記有機光電子素子用化合物は、電荷輸送物質またはホスト物質として使用されてもよく、熱分解温度(Td)は350〜600℃であってもよい。 The organic photoelectric child element compound may be used as a charge transporting material or the host material, the thermal decomposition temperature (T d) may be 350 to 600 ° C..
本発明の他の実施形態によれば、陽極、陰極、および前記陽極と陰極との間に配置された少なくとも1つの有機薄膜層を含み、前記有機薄膜層は、前記有機光電子素子用化合物を含む有機発光ダイオードを提供する。 According to another embodiment of the present invention, an anode, a cathode, and wherein comprises at least one organic thin layer disposed between the anode and the cathode, the organic thin film layer, the organic light electronic elements for compound An organic light emitting diode is provided.
前記有機薄膜層は、発光層、正孔阻止層、電子輸送層(ETL)、電子注入層(EIL)、正孔注入層(HIL)、正孔輸送層(HTL)、電子阻止層またはこれらの組み合わせであってもよい。 The organic thin film layer includes a light emitting layer, a hole blocking layer, an electron transport layer (ETL), an electron injection layer (EIL), a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer, or these It may be a combination.
本発明のさらなる他の実施形態によれば、前記有機発光ダイオードを含む表示装置が提供される。 According to still another embodiment of the present invention, a display device including the organic light emitting diode is provided.
その他本発明の実施形態の具体的な事項は以下の詳細な説明に記載されている。 Other specific matters of the embodiment of the present invention are described in the following detailed description.
本発明の一実施形態による有機光電子素子用化合物は、優れた熱的安定性を有し、特に、有機光電子素子の有機薄膜層に使用されて低い駆動電圧でも高い発光効率を有し、寿命が改善した有機光電子素子および表示装置を提供する。 Organic photoelectric child element compound according to an embodiment of the present invention has a superior thermal stability, especially, has a high luminous efficiency even at a low driving voltage is used in the organic thin film layer of an organic light electronic device, life to provide an organic light electronic device and a display device with improved.
以下、本発明の例示的な実施形態を詳しく説明する。但し、これらの実施形態は単なる例示であり、これらによって本発明が制限されるものではなく、特許請求の範囲の記載により定められる。 Hereinafter, exemplary embodiments of the present invention will be described in detail. However, these embodiments are merely examples, and the present invention is not limited thereto, and is defined by the description of the scope of claims.
本明細書で「置換された」の用語は、別途の定義がない限り、ハロゲン基、シアノ基、C1〜C30のアルキル基、C3〜C30のシクロアルキル基、C6〜C30のアリール基、C1〜C30のアルコキシ基またはこれらの組み合わせで置換されたものを意味する。 In the present specification, the term “substituted” is a halogen group, a cyano group, a C1-C30 alkyl group, a C3-C30 cycloalkyl group, a C6-C30 aryl group, a C1-C30 unless otherwise defined. A C30 alkoxy group or a combination thereof is meant.
本明細書で「ハロゲン基」の用語は、別途の定義がない限り、フルオロ基、クロロ基、ブロモ基またはこれらの組み合わせのハロゲン基を意味し、特に、フルオロ基を使用することが好ましい。 In this specification, the term “halogen group” means a halogen group of a fluoro group, a chloro group, a bromo group, or a combination thereof unless otherwise defined, and it is particularly preferable to use a fluoro group.
本明細書で「ヘテロ」の用語は、別途の定義がない限り、N、P、S、またはOを1〜3個含有し、残りは炭素であるものを意味する。 As used herein, the term “hetero” means one containing 1-3 N, P, S, or O, with the remainder being carbon, unless otherwise defined.
本明細書で「これらの組み合わせ」の用語は、別途の定義がない限り、2個以上の置換基が単結合で結合されていたり、2個以上の置換基が縮合して結合されているものを意味する。 In the present specification, the term “a combination thereof” means that two or more substituents are bonded by a single bond or two or more substituents are condensed and bonded unless otherwise defined. Means.
本発明の一実施形態によれば、下記の化学式1および2で表される置換基が結合された有機光電子素子用化合物が提供される。 According to an embodiment of the present invention, an organic photoelectric child element compound for the substituent is bonded to Formula 1 and 2 below are provided.
前記化学式1および2において、
Lは、2価〜7価の連結基であって、オキシド基、アミン基、ホスホニル基、ホスホネート基、スルホニル基、スルホネート基、置換されたまたは非置換のC1〜C30のアルキレン基、置換されたまたは非置換のC1〜C30のヘテロアルキレン基、置換されたまたは非置換のC3〜C30のシクロアルキレン基、置換されたまたは非置換のC1〜C30のヘテロシクロアルキレン基、置換されたまたは非置換のC6〜C30のアリーレン基、置換されたまたは非置換のC2〜C30のヘテロアリーレン基またはこれらの組み合わせである。この時、前記ヘテロシクロアルキレンの例としては、ピロリジン、テトラヒドロフラン、テトラヒドロチオフェン、ジオキサン、ジチアンなどの置換基が挙げられ、前記ヘテロアリーレンの例としては、チオフェン、フラン、ピロール、イミダゾール、チアゾール、オキサゾール、オキサジアゾール、チアジアゾール、トリアゾール、トリアジン、ピリジン、ピリミジン、ピリダジン、ピラジン、キノリン、イソキノリンなどの置換基が挙げられ、前記「これらの組み合わせ」に該当する置換基の例としては、カルバゾール、インドロカルバゾール、フルオレン、フルオレノン、ベンゾフラン、ベンゾチオフェン、ジベンゾフラン、ジベンゾチオフェン、オキサントレン、チアントレンなどの置換基が挙げられる。しかし、前記Lは前記例に限定されない。
In Formulas 1 and 2,
L is a divalent to 7-valent linking group, and is an oxide group, amine group, phosphonyl group, phosphonate group, sulfonyl group, sulfonate group, substituted or unsubstituted C1-C30 alkylene group, substituted Or an unsubstituted C1-C30 heteroalkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted A C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof. At this time, examples of the heterocycloalkylene include substituents such as pyrrolidine, tetrahydrofuran, tetrahydrothiophene, dioxane, dithiane, and examples of the heteroarylene include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, Substituents such as oxadiazole, thiadiazole, triazole, triazine, pyridine, pyrimidine, pyridazine, pyrazine, quinoline, isoquinoline, and the like. , Fluorene, fluorenone, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, oxanthrene, thianthrene and the like. However, L is not limited to the above example.
R1〜R5は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせであり、特に、前記R1およびR2は、互いに同一または異なるものであって、それぞれ独立して、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基またはこれらの組み合わせであり、R3〜R5は、互いに同一または異なるものであって、それぞれ独立して、水素、C1〜C30のアルキル基、C6〜C30のアリール基またはこれらの組み合わせであってもよい。 R 1 to R 5 are the same as or different from each other, and each independently represents hydrogen, a carbazolyl group, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C6- A C30 arylamine group or a combination thereof, in particular, the R 1 and R 2 are the same or different from each other, and each independently represents a carbazolyl group, a C1-C30 alkyl group, a C6-C30 An aryl group, a C2-C30 heteroaryl group, or a combination thereof, and R 3 to R 5 are the same or different from each other, and each independently represents hydrogen, a C1-C30 alkyl group, or a C6-C30. Or a combination thereof.
また、前記R1〜R5がC6〜C30のアリール基である場合、前記アリール基は、フェニル基、ナフチル基、アントラセン基、フェナントレン基、テトラセン基、ピレン基、フルオレン基またはこれらの組み合わせであってもよい。しかし、前記アリール基は前記例に限定されない。 When R 1 to R 5 are C6 to C30 aryl groups, the aryl group is a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a tetracene group, a pyrene group, a fluorene group, or a combination thereof. May be. However, the aryl group is not limited to the above example.
また、前記R1〜R5がC2〜C30のヘテロアリール基である場合、前記ヘテロアリール基は、チオフェン、フラン、ピロール、イミダゾール、チアゾール、オキサゾール、オキサジアゾール、チアジアゾール、トリアゾール、トリアジン、ピリジン、ピリミジン、ピリダジン、ピラジン、キノリン、イソキノリンまたはこれらの組み合わせであってもよい。しかし、前記ヘテロアリール基は前記例に限定されない。 When R 1 to R 5 are C2-C30 heteroaryl groups, the heteroaryl groups are thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, thiadiazole, triazole, triazine, pyridine, It may be pyrimidine, pyridazine, pyrazine, quinoline, isoquinoline or a combination thereof. However, the heteroaryl group is not limited to the above examples.
aは、2〜5の整数であり、この時、それぞれの反復単位は互いに同一または異なるものであってもよい。 a is an integer of 2 to 5, and each repeating unit may be the same as or different from each other.
前記化学式1は、下記の化学式1aで表されうる。 The chemical formula 1 may be represented by the following chemical formula 1a.
前記化学式1aにおいて、
Ra1およびRa2は、互いに同一または異なるものであって、それぞれ独立して、水素またはC1〜C10のアルキル基であり、
R3は、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせである。
In Formula 1a,
Ra 1 and Ra 2 are the same or different from each other, and each independently represents hydrogen or a C1-C10 alkyl group,
R 3 is hydrogen, a carbazolyl group, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C6-C30 arylamine group, or a combination thereof.
また、前記化学式2は、下記の化学式2a〜2cのいずれかで表されうる。 The chemical formula 2 may be represented by any of the following chemical formulas 2a to 2c.
前記化学式2a〜2cにおいて、
Lは、2価〜7価の連結基であって、オキシド基、アミン基、ホスホニル基、ホスホネート基、スルホニル基、スルホネート基、置換されたまたは非置換のC1〜C30のアルキレン基、置換されたまたは非置換のC1〜C30のヘテロアルキレン基、置換されたまたは非置換のC3〜C30のシクロアルキレン基、置換されたまたは非置換のC1〜C30のヘテロシクロアルキレン基、置換されたまたは非置換のC6〜C30のアリーレン基、置換されたまたは非置換のC2〜C30のヘテロアリーレン基またはこれらの組み合わせであり、
R4およびR5は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせであり、
aは、2〜5の整数である。
In the chemical formulas 2a to 2c,
L is a divalent to 7-valent linking group, and is an oxide group, amine group, phosphonyl group, phosphonate group, sulfonyl group, sulfonate group, substituted or unsubstituted C1-C30 alkylene group, substituted Or an unsubstituted C1-C30 heteroalkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted A C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof,
R 4 and R 5 are the same or different from each other, and are independently hydrogen, carbazolyl group, C1-C30 alkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, C6- An arylamine group of C30 or a combination thereof,
a is an integer of 2-5.
また、前記化学式2のLは、下記の化学式2d〜2jまたはこれらの組み合わせで表される化合物から誘導された2価〜7価の連結基でありうる。 In addition, L in Chemical Formula 2 may be a divalent to 7-valent linking group derived from a compound represented by the following Chemical Formulas 2d to 2j or a combination thereof.
前記化学式2d〜2jにおいて、
Q1〜Q6は、互いに同一または異なるものであって、それぞれ独立して、置換されたまたは非置換のN原子、置換されたまたは非置換のP原子、置換されたまたは非置換のS原子、置換されたまたは非置換のO原子、置換されたまたは非置換のC原子またはこれらの組み合わせであり、この時、前記置換は、水素、オキシド基、シアノ基、ハロゲン基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基またはこれらの組み合わせである。
In the chemical formulas 2d to 2j,
Q 1 to Q 6 are the same or different from each other, and each independently represents a substituted or unsubstituted N atom, a substituted or unsubstituted P atom, or a substituted or unsubstituted S atom. Substituted or unsubstituted O atom, substituted or unsubstituted C atom or a combination thereof, wherein the substitution is hydrogen, oxide group, cyano group, halogen group, C1-C30 alkyl A C6-C30 aryl group, a C2-C30 heteroaryl group, or a combination thereof.
前記化学式2において、aは、2または3であってもよい。 In the chemical formula 2, a may be 2 or 3.
また、前記化学式2のLは、前記化学式2kで表されてもよい。しかし、前記Lはこれらに限定されない。 In addition, L in the chemical formula 2 may be represented by the chemical formula 2k. However, the L is not limited to these.
また、前記有機光電子素子用化合物は、下記の化学式3〜化学式8で表されてもよい。 Moreover, the organic photoelectric child element compound may be represented by Formula 3 Formula 8 below.
前記化学式3〜8において、
Lは、2価〜7価の連結基であって、オキシド基、アミン基、ホスホニル基、ホスホネート基、スルホニル基、スルホネート基、置換されたまたは非置換のC1〜C30のアルキレン基、置換されたまたは非置換のC1〜C30のヘテロアルキレン基、置換されたまたは非置換のC3〜C30のシクロアルキレン基、置換されたまたは非置換のC1〜C30のヘテロシクロアルキレン基、置換されたまたは非置換のC6〜C30のアリーレン基、置換されたまたは非置換のC2〜C30のヘテロアリーレン基またはこれらの組み合わせであり、
R1〜R10は、互いに同一または異なるものであって、それぞれ独立して、水素、カルバゾリル基、C1〜C30のアルキル基、C6〜C30のアリール基、C2〜C30のヘテロアリール基、C6〜C30のアリールアミン基またはこれらの組み合わせである。
In the chemical formulas 3 to 8,
L is a divalent to 7-valent linking group, and is an oxide group, amine group, phosphonyl group, phosphonate group, sulfonyl group, sulfonate group, substituted or unsubstituted C1-C30 alkylene group, substituted Or an unsubstituted C1-C30 heteroalkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted A C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof,
R 1 to R 10 are the same as or different from each other, and each independently represents hydrogen, a carbazolyl group, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C6- A C30 arylamine group or a combination thereof.
また、前記有機光電子素子用化合物は、下記の化学式9〜化学式33で表されうる。しかし、前記有機光電子素子用化合物はこれらに限定されない。 Moreover, the organic photoelectric child element compound may be represented by Chemical Formula 9 to Formula 33 below. However, the organic photoelectric child element compound is not limited thereto.
前記有機光電子素子用化合物は、電荷輸送物質またはホスト物質として使用されてもよく、特に、前記有機光電子素子用化合物がホスト物質として使用される場合には燐光のホスト物質で、有機光電子素子の駆動電圧を下げ、発光効率を改善することができる。 The organic photoelectric child element compound may be used as a charge transporting material or the host material, in particular, the organic photoelectric child-element compound in the phosphorescent host material when used as a host material, an organic photoelectric child The driving voltage of the element can be lowered and the light emission efficiency can be improved.
また、前記有機光電子素子用化合物がホスト物質として使用される場合、前記有機光電子素子用化合物は当該分野で一般に使用される低分子ホスト物質または高分子ホスト物質と共に混合またはブレンドして使用してもよい。また、場合によってはポリビニルカルバゾール、ポリカーボネート、ポリエステル、ポリアリレート、ポリスチレン、アクリル高分子、メタクリル高分子、ポリブチラール、ポリビニルアセタール、フタル酸ジアリル高分子、フェノール樹脂、エポキシ樹脂、シリコン樹脂、ポリスルホン樹脂、またはウレア樹脂などのバインダー樹脂を混合して使用してもよい。 Further, when said organic photoelectric child-element compound is used as a host material, the organic photoelectric child element compound for use in mixing or blending with low molecular weight host material or polymeric host materials commonly used in the art May be. In some cases, polyvinyl carbazole, polycarbonate, polyester, polyarylate, polystyrene, acrylic polymer, methacrylic polymer, polybutyral, polyvinyl acetal, diallyl phthalate polymer, phenol resin, epoxy resin, silicone resin, polysulfone resin, or A binder resin such as a urea resin may be mixed and used.
例えば、前記低分子ホスト物質としては、下記の化学式34〜37で表される化合物を使用してもよく、高分子ホスト物質としては、フルオレン系高分子、ポリフェニレンビニレン系高分子、ポリパラフェニレン系高分子などの共役二重結合を有する高分子を使用してもよい。しかし、前記低分子ホスト物質および高分子ホスト物質は前記例に限定されない。 For example, as the low molecular weight host material, compounds represented by the following chemical formulas 34 to 37 may be used. As the polymeric host material, a fluorene polymer, a polyphenylene vinylene polymer, a polyparaphenylene polymer may be used. A polymer having a conjugated double bond such as a polymer may be used. However, the low molecular weight host material and the high molecular weight host material are not limited to the above examples.
また、前記有機光電子素子用化合物がホスト物質として使用される場合、前記有機光電子素子用化合物は、単独で使用してもよく、ドーパントと共に使用してもよい。前記ドーパントは、それ自体で発光能力の高い化合物であって通常、ホストに微量混合して使用されるため、これをゲストともいう。つまり、ドーパントはホスト物質にドーピングされて発光を起こす物質であって、一般に三重項状態以上に励起させる多重項励起によって発光する金属錯体のような物質が使用される。このようなドーパントとしては当該分野で一般に使用される赤色(R)、緑色(G)、青色(B)、白色(W)の蛍光または燐光ドーパントが全て使用可能であるが、特に、赤色、緑色、青色または白色の燐光ドーパントを使用することが好ましい。また、発光効率が高く、凝集が容易に行われず、ホスト物質に均一に分布されるものを使用してもよい。 Further, when said organic photoelectric child-element compound is used as a host material, the organic photoelectric child element compound may be used alone or may be used with the dopant. The dopant is a compound having a high light-emitting ability by itself and is usually used in a small amount mixed with the host, so that it is also called a guest. In other words, the dopant is a substance that emits light when doped with a host substance, and generally a substance such as a metal complex that emits light by multiplet excitation that excites the triplet state or higher is used. As such a dopant, red (R), green (G), blue (B), and white (W) fluorescent or phosphorescent dopants commonly used in the art can be used. It is preferred to use a blue or white phosphorescent dopant. Alternatively, a material that has high luminous efficiency, does not easily aggregate, and is uniformly distributed in the host material may be used.
前記燐光ドーパントの例としては、Ir、Pt、Os、Ti、Zr、Hf、Eu、Tb、Tm、Fe、Co、Ni、Ru、Rh、Pd、またはこれらの組み合わせである元素を含む有機金属化合物が挙げられる。より具体的に、赤色燐光ドーパントとしては、白金−オクタエチルポルフィリン錯体(PtOEP)、Ir(btp)2(acac)(ビス(2−(2’−ベンゾチエニル)−ピリジナト−N,C3’)イリジウム(アセチルアセトネート))、Ir(Piq)2(acac)、Ir(Piq)3、UDC社のRD61などを使用してもよく、緑色燐光ドーパントとしては、Ir(PPy)2(acac)、Ir(PPy)3、UDC社のGD48などを使用してもよく、青色燐光ドーパントとしては、(4,6−F2PPy)2Irpic、flrpic(イリジウム ビス[4,6−ジ−フルオロフェニル)−ピリジナト−N,C2’]ピコリネート)などを使用してもよい。この時、前記Piqは、1−フェニルイソキノリンを意味し、acacは、アセチルアセトネートを意味し、PPyは、2−フェニルピリジンを意味する。 Examples of the phosphorescent dopant include an organometallic compound containing an element that is Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. Is mentioned. More specifically, red phosphorescent dopants include platinum-octaethylporphyrin complex (PtOEP), Ir (btp) 2 (acac) (bis (2- (2′-benzothienyl) -pyridinato-N, C3 ′) iridium (Acetylacetonate)), Ir (Piq) 2 (acac), Ir (Piq) 3 , RD61 from UDC, etc. may be used, and as the green phosphorescent dopant, Ir (PPy) 2 (acac), Ir (PPy) 3 , GD48 manufactured by UDC may be used, and (4,6-F 2 PPy) 2 Irpic, flrpic (iridium bis [4,6-di-fluorophenyl)- Pyridinato-N, C2 ′] picolinate) and the like may be used. Here, Piq means 1-phenylisoquinoline, acac means acetylacetonate, and PPy means 2-phenylpyridine.
また、前記本発明の一実施形態による有機光電子素子用化合物は、熱分解温度(Td)が350〜600℃であってもよい。これによって、本発明の一実施形態による有機光電子素子用化合物は、熱的安定性に優れたホスト物質または電荷輸送物質として使用され得る。したがって、有機光電子素子の寿命特性を向上させることができる。 Moreover, the organic photoelectric child element compound according to an embodiment of the present invention, the thermal decomposition temperature (T d) may be 350 to 600 ° C.. Thus, the organic photoelectric child element compound according to an embodiment of the present invention can be used as a host material or a charge transport material having excellent thermal stability. Therefore, it is possible to improve the life characteristics of the organic photoelectric child elements.
本発明の他の実施形態によれば、陽極、陰極、および前記陽極と陰極との間に配置された有機薄膜層を含み、前記有機薄膜層は、本発明の一実施形態による有機光電子素子用化合物を含む有機光電子素子が提供される。この時、前記有機光電子素子は、有機発光ダイオード、有機太陽電池、有機トランジスタ、有機感光体ドラム、有機メモリ素子などが挙げられる。有機太陽電池の場合には、本発明の一実施形態による有機光電子素子用化合物が電極や電極バッファー層に含まれ、これによって量子効率を改善させることができ、有機トランジスタの場合には、ゲート、ソース−ドレイン電極などで電極物質として使用され得る。 According to another embodiment of the present invention, the anode comprises a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer, an organic light electronic device according to an embodiment of the present invention the organic light electronic device comprising the use compound. At this time, the organic light electronic device, organic light emitting diodes, organic solar cells, organic transistors, organic photosensitive drum, and an organic memory device. If organic solar cells, organic light electronic elements for compounds according to an embodiment of the present invention is contained in the electrode or the electrode buffer layer, whereby it is possible to improve the quantum efficiency, in the case of the organic transistor, the gate It can be used as an electrode material in source-drain electrodes and the like.
前記有機光電子素子用化合物を含むことができる有機薄膜層としては、発光層、正孔阻止層、電子輸送層(ETL)、電子注入層(EIL)、正孔注入層(HIL)、正孔輸送層(HTL)、電子阻止層またはこれらの組み合わせであってもよい。 The organic thin film layer may include an organic photoelectric child element compound, light-emitting layer, a hole blocking layer, electron transport layer (ETL), electron injection layer (EIL), hole injection layer (HIL), a hole It may be a transport layer (HTL), an electron blocking layer, or a combination thereof.
以下、有機発光ダイオードについて具体的に説明する。 Hereinafter, the organic light emitting diode will be described in detail.
図1〜図5は、前記有機光電子素子用化合物を含む有機発光ダイオードの断面図である。 Figures 1-5 are cross-sectional views of an organic light emitting diode including the organic photoelectric child element compound.
図1〜図5を参照すれば、有機発光ダイオード100、200、300、400、および500は、陽極120と陰極110との間に配置された少なくとも1層の有機薄膜層105を含む構造を有する。 1 to 5, the organic light emitting diodes 100, 200, 300, 400, and 500 have a structure including at least one organic thin film layer 105 disposed between the anode 120 and the cathode 110. .
有機発光ダイオードで使用される基板としては、当該分野において特に限定されないが、より具体的に、透明性、表面平滑性、取り扱いの容易性、および防水性に優れたガラス基板、透明プラスチック基板などの基板を使用することができる。 The substrate used in the organic light emitting diode is not particularly limited in the field, but more specifically, a glass substrate, a transparent plastic substrate, etc. that are excellent in transparency, surface smoothness, ease of handling, and waterproofness. A substrate can be used.
前記陽極120は、有機薄膜層へ正孔注入を円滑にするように仕事関数が大きい物質を含む。前記陽極物質の具体的な例としては、ニッケル、白金、バナジウム、クロム、銅、亜鉛、金などのような金属またはこれら金属の合金;酸化亜鉛、酸化インジウム、インジウムスズ酸化物(ITO)、インジウム亜鉛酸化物(IZO)などのような金属酸化物;ZnO/Al、SnO2/Sbなどのような金属酸化物と複合金属を使用することができる。但し、陽極は前記物質に限定されない。前記陽極は、より具体的に、ITOを含む透明電極を使用してもよい。 The anode 120 includes a material having a high work function so as to facilitate hole injection into the organic thin film layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys of these metals; zinc oxide, indium oxide, indium tin oxide (ITO), indium Metal oxides such as zinc oxide (IZO) and the like; metal oxides such as ZnO / Al, SnO 2 / Sb, and composite metals can be used. However, the anode is not limited to the above substance. More specifically, the anode may be a transparent electrode containing ITO.
前記陰極110は、有機薄膜層へ電子注入を円滑にするように仕事関数が小さい物質を含むことが好ましい。前記陰極物質の具体的な例としては、マグネシウム、カルシウム、ナトリウム、カリウム、チタン、インジウム、イットリウム、リチウム、ガドリニウム、アルミニウム、銀、スズ、鉛、セシウム、バリウムなどのような金属またはこれらの合金;LiF/Al、LiO2/Al、LiF/Ca、LiF/Al、BaF2/Caなどのような多層構造物質などが挙げられる。但し、陰極は前記物質に限定されない。前記陰極は、より具体的に、アルミニウムなどのような金属電極を使用してもよい。 The cathode 110 preferably includes a material having a low work function so as to facilitate electron injection into the organic thin film layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Examples thereof include multilayer structure materials such as LiF / Al, LiO 2 / Al, LiF / Ca, LiF / Al, BaF 2 / Ca, and the like. However, the cathode is not limited to the above substances. More specifically, the cathode may be a metal electrode such as aluminum.
まず、図1は、有機薄膜層105として発光層130のみが存在する有機発光ダイオード100を示した図面である。 First, FIG. 1 illustrates an organic light emitting diode 100 in which only the light emitting layer 130 exists as the organic thin film layer 105.
図2は、有機薄膜層105として電子輸送層(ETL)を含む発光層230と正孔輸送層(HTL)140が存在する2層型有機発光ダイオード200を示した図面である。この場合、発光層130は電子輸送層(ETL)の機能を果たし、正孔輸送層(HTL)140はITOのような透明電極との結合性および正孔輸送性を向上させる機能を果たす。 FIG. 2 shows a two-layer organic light emitting diode 200 having a light emitting layer 230 including an electron transport layer (ETL) and a hole transport layer (HTL) 140 as the organic thin film layer 105. In this case, the light emitting layer 130 functions as an electron transport layer (ETL), and the hole transport layer (HTL) 140 functions to improve the bonding property with a transparent electrode such as ITO and the hole transport property.
前記正孔輸送層(HTL)140は、当該分野で一般に使用されるものであって、その種類を特に限定しないが、例えば、ポリ(スチレンスルホン酸塩)(PSS)層でドーピングされたポリ(3,4−エチレンジオキシ−チオフェン)(PEDOT)(PEDOT:PSS)、N,N’−ビス(3−メチルフェニル)−N,N’−ジフェニル−[1,1’−ビフェニル]−4,4’−ジアミン(TPD)、N,N’−ジ(1−ナフチル)−N,N’−ジフェニルヘンジジン(NPB)などを本発明の一実施形態による有機光電子素子用化合物と共に使用することができる。但し、正孔輸送性物質は前記物質に限定されない。 The hole transport layer (HTL) 140 is commonly used in the art and is not particularly limited in type. For example, the hole transport layer (HTL) 140 may be a poly (styrene sulfonate) (PSS) layer doped with a poly (styrene (PSS) layer. 3,4-ethylenedioxy-thiophene) (PEDOT) (PEDOT: PSS), N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4, 4'-diamine (TPD), N, N'- di (1-naphthyl) -N, N'-diphenyl henge Jin (NPB) to be used in conjunction with organic photoelectric child element compound according to an embodiment of the present invention such as Can do. However, the hole transporting substance is not limited to the above substance.
図3は、有機薄膜層105として電子輸送層(ETL)150、発光層130、および正孔輸層(HTL)140が存在する3層型有機発光ダイオード300を示した図面であり、前記発光層130は独立した形態となっており、電子輸送性や正孔輸送性に優れた膜を別途の層で積層した形態を示している。 FIG. 3 shows a three-layer organic light emitting diode 300 having an electron transport layer (ETL) 150, a light emitting layer 130, and a hole transport layer (HTL) 140 as the organic thin film layer 105. Reference numeral 130 is an independent form, and shows a form in which a film excellent in electron transporting property and hole transporting property is laminated in a separate layer.
前記電子輸送層(ETL)150は、当該分野で一般に使用されるものであって、特に限定されないが、例えば、アルミニウムトリス(8−ヒドロキシキノリン)(Alq3);2−(4−ビフェニル−5−フェニル−1,3,4−オキサジアゾール(PBD)のような1,3,4−オキサジアゾール誘導体;1,3,4−トリス[(3−フェニル−6−トリフルオロメチル)キノキサリン−2−イル]ベンゼン(TPQ)のようなキノキサリン誘導体;およびトリアゾール誘導体などを本発明の一実施形態による有機光電子素子用化合物と共に使用してもよい。但し、電子輸送性物質は前記物質に限定されない。 The electron transport layer (ETL) 150 is generally used in the art and is not particularly limited. For example, aluminum tris (8-hydroxyquinoline) (Alq 3 ); 2- (4-biphenyl-5 -1,3,4-oxadiazole derivatives such as phenyl-1,3,4-oxadiazole (PBD); 1,3,4-tris [(3-phenyl-6-trifluoromethyl) quinoxaline- 2-yl] quinoxaline derivative such as benzene (TPQ);. and triazole derivatives such as may be used with an organic photoelectric child element compound according to an embodiment of the present invention, however, the electron transporting material is limited to the material Not.
図4は、有機薄膜層105として電子注入層(EIL)160、発光層130、正孔輸送層(HTL)140、および正孔注入層(HIL)170が存在する4層型有機発光ダイオード400を示した図面であり、前記正孔注入層(HIL)170は陰極として使用されるITOとの結合性を向上させることができる。 FIG. 4 shows a four-layer organic light emitting diode 400 in which an electron injection layer (EIL) 160, a light emitting layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170 exist as the organic thin film layer 105. In the drawing, the hole injecting layer (HIL) 170 can improve the bonding with ITO used as a cathode.
図5は、有機薄膜層105として電子輸送層(ETL)150、発光層130、正孔輸送層(HTL)140、および正孔注入層(HIL)170にさらに電子注入層(EIL)160が存在する5層型有機発光ダイオード500を示した図面であり、前記有機発光ダイオード500は低電圧化に効果的である。 FIG. 5 shows that the electron transport layer (ETL) 150, the light emitting layer 130, the hole transport layer (HTL) 140, and the hole injection layer (HIL) 170 as the organic thin film layer 105 further include an electron injection layer (EIL) 160. it is a view showing a 5-layer type organic light-emitting diode 500, the organic light emitting diode 500 is effective for a reduction in voltage.
前記発光層130、230の厚さは、5〜1000nmであってもよく、前記正孔輸送層(HTL)140、および電子輸送層(ETL)150の厚さは、それぞれ独立して、10〜10,000Åであってもよい。しかし、前記厚さ範囲に限定されない。 The light emitting layers 130 and 230 may have a thickness of 5 to 1000 nm, and the hole transport layer (HTL) 140 and the electron transport layer (ETL) 150 may each independently have a thickness of 10 to 10 nm. It may be 10,000cm. However, the thickness range is not limited.
前記図1〜図5において前記有機薄膜層105をなす電子輸送層(ETL)150、電子注入層(EIL)160、発光層130、230、正孔輸送層(HTL)140、正孔注入層(HIL)170またはこれらの組み合わせには本発明の一実施形態による有機光電子素子用化合物が含まれてもよい。この時、前記有機光電子素子用化合物は、電子輸送層(ETL)150または電子注入層(EIL)160を含む電子輸送層(ETL)150に使用されてもよく、その中でも電子輸送層(ETL)に含まれる場合、正孔阻止層を別途に形成する必要がないため、より単純化した構造の有機発光ダイオードを提供することができる。 1 to 5, the electron transport layer (ETL) 150, the electron injection layer (EIL) 160, the light emitting layers 130 and 230, the hole transport layer (HTL) 140, the hole injection layer ( HIL) 170 or may be included organic photoelectric child element compound according to an embodiment of the present invention to a combination thereof. At this time, the organic photoelectric child element compound, the electron transport layer (ETL) 0.99 or an electron injection layer (EIL) 160 may be used in the electron transport layer (ETL) 0.99 containing, electron-transporting layer among them (ETL ), It is not necessary to form a hole blocking layer separately, and thus an organic light emitting diode having a more simplified structure can be provided.
また、前記有機光電子素子用化合物が発光層130、230内に含まれる場合、前記有機光電子素子用化合物は燐光ホストとして使用され得、前記発光層130、230はドーパントをさらに含むことができる。この時、前記ドーパントは、赤色、緑色、青色、または白色の燐光ドーパントであってもよい。 Further, when said organic photoelectric child-element compounds are included in the light emitting layer 130 and 230, the organic photoelectric child element compound is used as the phosphorescent host obtained, the light emitting layer 130, 230 may further include a dopant . At this time, the dopant may be a red, green, blue, or white phosphorescent dopant.
前述した有機発光ダイオードは、基板に陽極を形成した後、真空蒸着法、スパッタリング、プラズマメッキ、イオンメッキなどのような乾式成膜法;スピンコーティング、浸漬法、流動コーティング法などのような湿式成膜法などで有機薄膜層を形成した後、その上に陰極を形成して製造してもよい。 The organic light-emitting diode described above is formed by forming an anode on a substrate, and then forming a dry film formation method such as vacuum deposition, sputtering, plasma plating, ion plating, etc .; After the organic thin film layer is formed by a film method or the like, the cathode may be formed thereon for manufacturing.
本発明のさらなる他の一実施形態によれば、前記有機発光ダイオードを含む表示装置が提供される。 According to still another embodiment of the present invention, a display device including the organic light emitting diode is provided.
以下の実施を用いて本発明をより詳細に説明する。但し、これらの実施例は例示的な実施形態であって、本発明は制限されない。 The invention is explained in more detail using the following implementation. However, these examples are exemplary embodiments and the present invention is not limited.
(有機光電子素子用化合物の合成)
実施例1
有機光電子素子用化合物を、下記の反応式1の方法で合成した。
(Synthesis of organic photoelectric child element compound)
Example 1
The organic photoelectric child element compound was synthesized in Scheme 1 of the following methods.
第1段階:中間体生成物(B)の合成
アルゴン雰囲気で温度計、還流コンデンサ、および攪拌機付き500mLの丸底フラスコに化合物A11.0g(24.7mmol)、1−ブロモ−2−ニトロベンゼン6.0g(29.7mmol)、テトラキストリフェニルホスフィンパラジウム1g(0.86mmol)、および200mLのテトラヒドロフランを混合し、前記混合溶液に2Mの炭酸カリウム50mLを入れた後、75℃で24時間攪拌した。
First Step: Synthesis of Intermediate Product (B) In a 500 mL round bottom flask equipped with a thermometer, reflux condenser and stirrer in an argon atmosphere, 11.0 g (24.7 mmol) of compound A, 1-bromo-2-nitrobenzene 0 g (29.7 mmol), 1 g (0.86 mmol) of tetrakistriphenylphosphine palladium, and 200 mL of tetrahydrofuran were mixed, 50 mL of 2M potassium carbonate was added to the mixed solution, and the mixture was stirred at 75 ° C. for 24 hours.
室温に冷却して前記反応物の反応を終結した後、塩化メチレンで抽出し、水で洗浄した。その後、無水硫酸マグネシウムで反応物の水分を除去し、ろ過することによって有機溶媒を除去した。最終残留物は塩化メチレンとヘキサンとの混合溶媒(体積比1:1)を使用するシリカゲルクロマトグラフィーで精製して中間体生成物(B)を9g(収率:82.7%)得た。 After cooling to room temperature to complete the reaction of the reactant, it was extracted with methylene chloride and washed with water. Then, the water | moisture content of the reaction material was removed with anhydrous magnesium sulfate, and the organic solvent was removed by filtering. The final residue was purified by silica gel chromatography using a mixed solvent of methylene chloride and hexane (volume ratio 1: 1) to obtain 9 g of intermediate product (B) (yield: 82.7%).
第2段階:中間体生成物(C)の合成
前記第1段階で合成された中間体生成物(B)8g(18.2mmol)およびトリフェニルホスフィン14.3g(54.6mmol)をジクロロベンゼン150mlに溶解し、アルゴン雰囲気下で160℃で加熱還流した。
Second stage: Synthesis of intermediate product (C) 8 g (18.2 mmol) of the intermediate product (B) synthesized in the first stage and 14.3 g (54.6 mmol) of triphenylphosphine were added to 150 ml of dichlorobenzene. And heated to reflux at 160 ° C. under an argon atmosphere.
有機溶媒を減圧下で蒸留して除去した後、塩化メチレンで抽出し、水で洗浄した。その後、洗浄した反応物を無水硫酸マグネシウムで反応物の水分を除去し、ろ過することによって有機溶媒を除去した。最終残留物は塩化メチレンとヘキサンとの混合溶媒(体積比2:1)を使用するシリカゲルクロマトグラフィーで精製して中間体生成物(C)を5.3g(収率:71.5%)得た。 The organic solvent was removed by distillation under reduced pressure, followed by extraction with methylene chloride and washing with water. Then, the organic solvent was removed by removing the water | moisture content of the reaction material with the anhydrous magnesium sulfate, and filtering the wash | cleaned reaction material. The final residue was purified by silica gel chromatography using a mixed solvent of methylene chloride and hexane (volume ratio 2: 1) to obtain 5.3 g of intermediate product (C) (yield: 71.5%). It was.
第3段階:有機光電子素子用化合物の合成
前記第2段階で合成された中間体生成物(C)5g(12.2mmol)を無水テトラヒドロフラン100mLに溶かした後、−78℃で1.6Mのn−BuLi9.2mLを徐々に滴下し、30分間攪拌した。次に、室温で20分間さらに攪拌し、再び−78℃で2,4−ジクロロ−6−フェニルトリアジン1.32g(5.8mmol)と混合して室温で12時間攪拌した。
Stage 3: After dissolving intermediate product synthesized in Synthesis said second stage of the organic light electronic elements for compound (C) 5g (12.2mmol) in anhydrous tetrahydrofuran 100 mL, in 1.6M at -78 ° C. 9.2 mL of n-BuLi was gradually added dropwise and stirred for 30 minutes. Next, the mixture was further stirred at room temperature for 20 minutes, mixed again with 1.32 g (5.8 mmol) of 2,4-dichloro-6-phenyltriazine at −78 ° C., and stirred at room temperature for 12 hours.
室温に冷却して前記反応物の反応を終結した後、塩化メチレンで抽出し、水で洗浄した。その後、無水硫酸マグネシウムで反応物の水分を除去し、ろ過することによって有機溶媒を除去した。最終残留物は塩化メチレンとヘキサンとの混合溶媒(体積比1:3)を使用するシリカゲルクロマトグラフィーで精製し、再結晶して有機光電子素子用化合物2.7g(収率:48.0%)を得た。 After cooling to room temperature to complete the reaction of the reactant, it was extracted with methylene chloride and washed with water. Then, the water | moisture content of the reaction material was removed with anhydrous magnesium sulfate, and the organic solvent was removed by filtering. The final residue was mixed solvent (volume ratio 1: 3) of methylene chloride and hexane and purified by silica gel chromatography using, recrystallized organic photoelectric child element compound 2.7 g (yield: 48.0% )
前記得られた有機光電子素子用化合物を元素分析で分析した結果は次のとおりである。 As a result of analyzing the obtained organic photoelectric child element compound by elemental analysis is as follows.
計算値 C,88.08;H,4.68,N,7.23
実測値 C,88.10;H,4.66,N,7.23
実施例2
有機光電子素子用化合物を、下記の反応式2の方法で合成した。
Calculated value C, 88.08; H, 4.68, N, 7.23
Found C, 88.10; H, 4.66, N, 7.23
Example 2
The organic photoelectric child element compound was synthesized in Scheme 2 the following methods.
第1段階:中間体生成物(E)の合成
アルゴン雰囲気で温度計、還流コンデンサ、および攪拌機付き500mLの丸底フラスコに化合物D10.0g(22.5mmol)、1−ブロモ−2−ニトロベンゼン5.45g(27.0mmol)、テトラキストリフェニルホスフィンパラジウム1g(0.86mmol)および200mLのテトラヒドロフランを混合し、前記混合溶液に20%濃度のテトラトリエチルアンモニウムヒドロキシド50mLを入れた後、75℃で24時間攪拌した。
First Step: Synthesis of Intermediate Product (E) 10.0 g (22.5 mmol) of compound D, 1-bromo-2-nitrobenzene in a 500 mL round bottom flask with thermometer, reflux condenser, and stirrer in an argon atmosphere. 45 g (27.0 mmol), 1 g (0.86 mmol) of tetrakistriphenylphosphine palladium and 200 mL of tetrahydrofuran were mixed, and 50 mL of 20% tetratriethylammonium hydroxide was added to the mixed solution, and then at 75 ° C. for 24 hours. Stir.
室温に冷却して前記反応物の反応を終結した後、塩化メチレンで抽出し、水で洗浄した。その後、無水硫酸マグネシウムで反応物の水分を除去し、ろ過することによって有機溶媒を除去した。最終残留物は塩化メチレンとヘキサンとの混合溶媒(体積比1:1)を使用するシリカゲルクロマトグラフィーで精製して中間体生成物(E)を7.8g(収率:78.8%)得た。 After cooling to room temperature to complete the reaction of the reactant, it was extracted with methylene chloride and washed with water. Then, the water | moisture content of the reaction material was removed with anhydrous magnesium sulfate, and the organic solvent was removed by filtering. The final residue was purified by silica gel chromatography using a mixed solvent of methylene chloride and hexane (volume ratio 1: 1) to obtain 7.8 g of intermediate product (E) (yield: 78.8%). It was.
第2段階:中間体生成物(F)の合成
前記第1段階で合成された中間体生成物(E)7g(15.9mmol)およびトリフェニルホスフィン14.3g(54.6mmol)をジクロロベンゼン150mlに溶解し、アルゴン雰囲気下で160℃で加熱還流した。
Second Step: Synthesis of Intermediate Product (F) 7 g (15.9 mmol) of the intermediate product (E) synthesized in the first step and 14.3 g (54.6 mmol) of triphenylphosphine were added to 150 ml of dichlorobenzene. And heated to reflux at 160 ° C. under an argon atmosphere.
有機溶媒を減圧下で蒸留して除去した後、塩化メチレンで抽出し、水で洗浄した。その後、無水硫酸マグネシウムで洗浄した反応物の水分を除去し、ろ過することによって有機溶媒を除去した。最終残留物は塩化メチレンとヘキサンとの混合溶媒(体積比2:1)を使用するシリカゲルクロマトグラフィーで精製して中間体生成物(F)を4.4g(収率:68%)得た。 The organic solvent was removed by distillation under reduced pressure, followed by extraction with methylene chloride and washing with water. Thereafter, the water content of the reaction product washed with anhydrous magnesium sulfate was removed, and the organic solvent was removed by filtration. The final residue was purified by silica gel chromatography using a mixed solvent of methylene chloride and hexane (volume ratio 2: 1) to obtain 4.4 g of intermediate product (F) (yield: 68%).
第3段階:有機光電子素子用化合物の合成
前記第2段階で合成された中間体生成物(F)4g(9.8mmol)を無水テトラヒドロフラン100mLに溶かした後、−78℃で1.6Mのn−BuLi9.2mLを徐々に滴下し、30分間攪拌した。次に、室温で20分間さらに攪拌し、再び−78℃で2,4−ジクロロ−6−フェニルトリアジン1g(4.4mmol)と混合して室温で12時間攪拌した。
Stage 3: After dissolving intermediate product synthesized in Synthesis said second stage of the organic light electronic elements for compound (F) 4g (9.8mmol) in anhydrous tetrahydrofuran 100 mL, in 1.6M at -78 ° C. 9.2 mL of n-BuLi was gradually added dropwise and stirred for 30 minutes. Next, the mixture was further stirred at room temperature for 20 minutes, again mixed with 1 g (4.4 mmol) of 2,4-dichloro-6-phenyltriazine at −78 ° C., and stirred at room temperature for 12 hours.
室温に冷却して前記反応物の反応を終結した後、塩化メチレンで抽出し、水で洗浄した。その後、無水硫酸マグネシウムで反応物の水分を除去し、ろ過することによって有機溶媒を除去した。最終残留物は塩化メチレンとヘキサンとの混合溶媒(体積比1:3)を使用するシリカゲルクロマトグラフィーで精製し、再結晶して有機光電子素子用化合物1.8g(収率:42.3%)を得た。 After cooling to room temperature to complete the reaction of the reactant, it was extracted with methylene chloride and washed with water. Then, the water | moisture content of the reaction material was removed with anhydrous magnesium sulfate, and the organic solvent was removed by filtering. The final residue mixed solvent of methylene chloride and hexane (volume ratio 1: 3) was purified by silica gel chromatography using, recrystallized organic photoelectric child element compound 1.8 g (yield: 42.3% )
前記得られた有機光電子素子用化合物を元素分析で分析した結果は次のとおりである。 As a result of analyzing the obtained organic photoelectric child element compound by elemental analysis is as follows.
計算値 C,88.08;H,4.68,N,7.23
実測値 C,88.06;H,4.70,N,7.23
(有機発光ダイオードの製造)
実施例3
前記実施例1で合成された化合物をホストとして使用し、Ir(PPy)3をドーパントとして使用して有機発光ダイオードを製作した。陽極としてはITOを1000Åの厚さで使用し、陰極としてはアルミニウム(Al)を1500Åの厚さで使用した。
Calculated value C, 88.08; H, 4.68, N, 7.23
Found C, 88.06; H, 4.70, N, 7.23
(Manufacture of organic light emitting diodes)
Example 3
An organic light emitting diode was fabricated using the compound synthesized in Example 1 as a host and Ir (PPy) 3 as a dopant. ITO was used as the anode with a thickness of 1000 mm, and aluminum (Al) was used as the cathode with a thickness of 1500 mm.
具体的に、有機発光ダイオードの製造方法を説明すれば、陽極は15Ω/cm2の面抵抗値を有するITOガラス基板を50mm×50mm×0.7mmの大きさに切断し、アセトンとイソプロピルアルコールと純水の中で各15分間超音波洗浄した後、30分間UVオゾン洗浄して製造した。 Specifically, a method of manufacturing an organic light emitting diode will be described. An anode is formed by cutting an ITO glass substrate having a sheet resistance value of 15 Ω / cm 2 into a size of 50 mm × 50 mm × 0.7 mm, and acetone and isopropyl alcohol. After ultrasonic cleaning for 15 minutes in pure water, UV ozone cleaning was performed for 30 minutes.
前記基板上部に真空度650×10−7Pa、蒸着速度0.1〜0.3nm/sの条件でN,N'−ジ(1−ナフチル)−N,N'−ジフェニルベンジジン(NPB)(70nm)および4,4',4”−トリ(N−カルバゾリル)トリフェニルアミン(TCTA)(10nm)を蒸着して800Åの正孔輸送層(HTL)を形成した。 N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine (NPB) (NPB) under the conditions of a vacuum degree of 650 × 10 −7 Pa and a deposition rate of 0.1 to 0.3 nm / s on the substrate. 70 nm) and 4,4 ′, 4 ″ -tri (N-carbazolyl) triphenylamine (TCTA) (10 nm) were deposited to form an 800 正 孔 hole transport layer (HTL).
次に、同様の真空蒸着条件で前記実施例1で合成された化合物を利用して膜厚300Åの発光層を形成し、この時、燐光ドーパントであるIr(PPy)3を同時に蒸着した。この時、燐光ドーパントの蒸着速度を調節し、発光層の全体量を100重量%とした時、燐光ドーパントが合計10重量%になるように蒸着した。 Next, a light-emitting layer having a thickness of 300 mm was formed using the compound synthesized in Example 1 under the same vacuum deposition conditions. At this time, Ir (PPy) 3 as a phosphorescent dopant was simultaneously deposited. At this time, the deposition rate of the phosphorescent dopant was adjusted, and when the total amount of the light emitting layer was 100% by weight, the phosphorescent dopant was deposited so that the total amount was 10% by weight.
前記発光層上部に同様の真空蒸着条件を利用してビス(8−ヒドロキシ−2−メチルキノリナト)−アルミニウムビフェノキシド(BAlq)を蒸着して膜厚50Åの正孔阻止層を形成した。 Bis (8-hydroxy-2-methylquinolinato) -aluminum biphenoxide (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 mm.
次に、同様の真空蒸着条件でAlq3を蒸着し、膜厚200Åの電子輸送層(ETL)を形成した。 Next, Alq 3 was deposited under the same vacuum deposition conditions to form an electron transport layer (ETL) having a thickness of 200 mm.
前記電子輸送層(ETL)上部に陰極としてLiFとAlを順次に蒸着して有機発光ダイオードを製作した。 An organic light emitting diode was manufactured by sequentially depositing LiF and Al as a cathode on the electron transport layer (ETL).
前記有機発光ダイオードは、ITO/NPB(70nm)/TCTA(10nm)/EML(実施例1の化合物(90重量%)+Ir(PPy)3(10重量%)、30nm)/Balq(5nm)/Alq3(20nm)/LiF(0.5nm)/Al(150nm)の構造で製作した。 The organic light emitting diode is ITO / NPB (70 nm) / TCTA (10 nm) / EML (the compound of Example 1 (90 wt%) + Ir (PPy) 3 (10 wt%), 30 nm) / Balq (5 nm) / Alq. 3 (20 nm) / LiF (0.5 nm) / Al (150 nm).
比較例1
前記実施例1で合成された化合物の代わりに、4,4’−N,N’−ジカルバゾールビフェニル(CBP)を発光層のホストとして使用したことを除いては前記実施例3と同様な方法で有機発光ダイオードを製作した。
Comparative Example 1
The same method as in Example 3 except that 4,4′-N, N′-dicarbazole biphenyl (CBP) was used as the host of the light emitting layer instead of the compound synthesized in Example 1. Made an organic light-emitting diode.
実験例1:有機発光ダイオードの性能評価
前記実施例3および比較例1で製作された有機発光ダイオードに対して電圧による電流密度の変化、輝度の変化および発光効率を測定した。具体的な測定方法は次のとおりであり、その結果は下記表1に示した。
Experimental Example 1: Performance Evaluation of Organic Light-Emitting Diode The organic light-emitting diode manufactured in Example 3 and Comparative Example 1 was measured for changes in current density, luminance, and luminous efficiency due to voltage. The specific measurement method is as follows, and the results are shown in Table 1 below.
(1)電圧変化による電流密度の変化の測定
電圧を0Vから10Vまで上昇させながら電流−電圧計(Keithley 2400)を利用して電流値を測定し、測定された電流値を面積で割って電流密度を計算した。その結果を図6に示した。
(1) Measurement of change in current density due to voltage change The current value is measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value is divided by the area to obtain the current. Density was calculated. The results are shown in FIG.
(2)電圧変化による輝度の変化の測定
製造された有機発光ダイオードに対して、電圧を0Vから10Vまで上昇させながら輝度計(Minolta Cs−1000A)を利用して輝度を測定して結果を得た。その結果を図7に示した。
(2) Measurement of luminance change due to voltage change For the manufactured organic light emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the result was obtained. It was. The results are shown in FIG.
(3)発光効率の測定
前記(1)および(2)で測定された輝度と電流密度および電圧を利用して同一の明るさ(2000cd/m2)の電流効率(cd/A)および電力効率(lm/W)を計算した。その結果を図8および9に示した。
(3) Measurement of luminous efficiency Current efficiency (cd / A) and power efficiency of the same brightness (2000 cd / m 2 ) using the luminance, current density and voltage measured in (1) and (2) above (Lm / W) was calculated. The results are shown in FIGS.
(4)色座標
輝度計(Minolta Cs−100A)を利用して色座標を測定し、その結果を下記表1に示した。
(4) Color coordinates Color coordinates were measured using a luminance meter (Minolta Cs-100A), and the results are shown in Table 1 below.
前記表1を参照すれば、有機発光ダイオードの特性評価結果、実施例3で製造された有機発光ダイオードは比較例1の有機発光ダイオードに比べて、駆動電圧は低く、電流効率および電力効率は極めて改善された素子性能を示すことを確認することができた。前記実施例1による化合物は有機発光ダイオードの駆動電圧を下げ、輝度と効率を向上させることを確認することができた。 Referring to Table 1, as a result of evaluating the characteristics of the organic light emitting diode, the organic light emitting diode manufactured in Example 3 has a lower driving voltage than the organic light emitting diode of Comparative Example 1, and has extremely high current efficiency and power efficiency. It was confirmed that the device performance was improved. It was confirmed that the compound according to Example 1 lowered the driving voltage of the organic light emitting diode and improved the luminance and efficiency.
本発明は、現在考えられる実施例に基づき記載されているが、本発明は前記実施例に限定されるものではなく、特許請求の範囲の精神および範囲に含まれる多様な変形および等価の形態で行われうる。したがって、上記の実施例は例示的なものであり、本発明をいかようにも限定するものではないことを理解しなければならない。 Although the present invention has been described based on the presently considered embodiments, the present invention is not limited to the embodiments described above, and various modifications and equivalent forms included in the spirit and scope of the claims. Can be done. Therefore, it should be understood that the above examples are illustrative and do not limit the invention in any way.
100、200、300、400、500 有機発光ダイオード、
105 有機薄膜層、
110 陰極、
120 陽極、
130 発光層、
140 正孔輸送層(HTL)、
150 電子輸送層(ETL)、
160 電子注入層(EIL)、
170 正孔注入層(HIL)、
230 発光層+電子輸送層(ETL)。
100, 200, 300, 400, 500 organic light emitting diodes ,
105 organic thin film layer,
110 cathode,
120 anode,
130 light emitting layer,
140 hole transport layer (HTL),
150 electron transport layer (ETL),
160 electron injection layer (EIL),
170 hole injection layer (HIL),
230 Light emitting layer + electron transport layer (ETL).
Claims (11)
Lは、2価の連結基であって、C1〜C30のアルキル基またはC6〜C30のアリール基で置換されたまたは非置換の、1〜3個の窒素原子のみをヘテロ原子として含むC2〜C30のヘテロアリーレン基であり、
R1およびR2は、互いに同一または異なるものであって、それぞれ独立して、C1〜C30のアルキル基またはC6〜C30のアリール基で置換されたまたは非置換のC6〜C30のアリール基であり、
R3〜R5は、すべて水素であり、
aは、2である。 Compound for organic optoelectronic device to which substituents represented by the following chemical formula 1 and chemical formula 2 are bonded :
L is a divalent linking group, which is substituted or unsubstituted with a C1 to C30 alkyl group or a C6 to C30 aryl group, and contains only 1 to 3 nitrogen atoms as C2 to C30. A heteroarylene group of
R 1 and R 2 are the same or different from each other, and each independently represent a C1-C30 alkyl group or a C6-C30 aryl group substituted or unsubstituted C6-C30 aryl group ,
R 3 to R 5 are all hydrogen,
a is 2 .
Ra1およびRa2は、すべて水素であり、
R3は、水素である。 The compound for an organic optoelectronic device according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1a:
Ra 1 and Ra 2 are all hydrogen,
R 3 is hydrogen.
Lは、2価の連結基であって、C1〜C30のアルキル基またはC6〜C30のアリール基で置換されたまたは非置換の、1〜3個の窒素原子のみをヘテロ原子として含むC2〜C30のヘテロアリーレン基であり、
R4およびR5は、すべて水素であり、
aは、2である。 The chemical formula 2 is represented by any one of the following chemical formulas 2a to 2c, and the compound for an organic optoelectronic device according to claim 1 or 2 :
L is a divalent linking group, which is substituted or unsubstituted with a C1 to C30 alkyl group or a C6 to C30 aryl group, and contains only 1 to 3 nitrogen atoms as C2 to C30. A heteroarylene group of
R 4 and R 5 are all hydrogen,
a is 2 .
Q1〜Q6は、互いに同一または異なるものであって、それぞれ独立して、N原子、または置換されたもしくは非置換のC原子であり、この時、前記置換は、C6〜C30のアリール基であり、Q 1 〜Q 6 のうち1〜3個はN原子であり、残りはC原子である。 The compound for organic optoelectronic devices according to any one of claims 1 to 3, wherein L in the chemical formula 2 is a divalent linking group derived from a compound represented by the following chemical formula 2e:
Q 1 to Q 6 are the same or different from one another, each independently, an N atom or a substituted or unsubstituted C atom, when this, the substitution, aryl of C6~C30 Motodea is, 1-3 of Q 1 to Q 6 is a N atom, the remainder being C atoms.
Lは、C1〜C30のアルキル基またはC6〜C30のアリール基で置換されたまたは非置換の、1〜3個の窒素原子のみをヘテロ原子として含むC2〜C30のヘテロアリーレン基であり、
R1、R2、R6およびR7は、互いに同一または異なるものであって、それぞれ独立して、C1〜C30のアルキル基またはC6〜C30のアリール基で置換されたまたは非置換のC6〜C30のアリール基であり、
R3〜R5およびR8〜R10は、すべて水素である。 The compound for organic optoelectronic devices according to claim 1, represented by any one of the following chemical formulas 3 to 8:
L is a C2 to C30 heteroarylene group containing only 1 to 3 nitrogen atoms as a heteroatom, substituted or unsubstituted with a C1 to C30 alkyl group or a C6 to C30 aryl group ,
R 1 , R 2 , R 6 and R 7 are the same or different from each other, and each independently represents a C1-C30 alkyl group substituted or unsubstituted with a C1-C30 alkyl group or a C6-C30 aryl group. An aryl group of C30,
R 3 to R 5 and R 8 to R 10 are all hydrogen.
前記少なくとも1つの有機薄膜層は、請求項1〜7のいずれか1項に記載の有機光電子素子用化合物を含む、有機発光ダイオード。 An anode; a cathode; and at least one organic thin film layer disposed between the anode and the cathode;
Wherein said at least one organic thin film layer comprises a compound for an organic optoelectronic device according to any one of claims 1 to 7 OLED.
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009031021A1 (en) * | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20110009920A (en) * | 2009-07-23 | 2011-01-31 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
KR101063940B1 (en) * | 2009-08-26 | 2011-09-08 | 주식회사 두산 | Novel organic compound and organic light emitting device using same |
WO2012026780A1 (en) * | 2010-08-27 | 2012-03-01 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
JP5699581B2 (en) * | 2010-12-15 | 2015-04-15 | Jnc株式会社 | Fused pyrrole polycyclic compound, material for light emitting layer, and organic electroluminescent device using the same |
KR20130011405A (en) * | 2011-07-21 | 2013-01-30 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
KR101954980B1 (en) * | 2011-11-03 | 2019-05-31 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light-emitting diode comprising the same |
KR101803537B1 (en) * | 2012-02-09 | 2017-11-30 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Light-emitting element |
KR101897052B1 (en) * | 2012-04-13 | 2018-09-12 | 에스에프씨 주식회사 | Fused cyclic compound and organoelectroluminescent device comprising the compound |
GB201208793D0 (en) | 2012-05-18 | 2012-07-04 | Isis Innovation | Optoelectronic device |
EP2850669B1 (en) | 2012-05-18 | 2016-02-24 | Isis Innovation Limited | Photovoltaic device comprising perovskites |
PL2850627T3 (en) | 2012-05-18 | 2016-10-31 | Optoelectronic device comprising porous scaffold material and perovskites | |
KR102038815B1 (en) | 2012-07-31 | 2019-10-31 | 엘지디스플레이 주식회사 | Host compound for phosphorescent dopant and organic light emitting diode device using the same |
KR102029336B1 (en) | 2012-08-21 | 2019-10-07 | 제일모직 주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
KR102607292B1 (en) | 2012-09-18 | 2023-11-29 | 옥스포드 유니버시티 이노베이션 리미티드 | Optoelectonic device |
KR102052739B1 (en) * | 2012-12-26 | 2019-12-06 | 엘지디스플레이 주식회사 | Phophorescene compounds and organic light emitting diode devices using the same |
WO2015099438A1 (en) * | 2013-12-27 | 2015-07-02 | 주식회사 두산 | Organic light-emitting compound and organic electroluminescent element using same |
KR102626916B1 (en) * | 2015-09-09 | 2024-01-19 | 삼성전자주식회사 | Condensed cyclic compound and organic light emitting device including the same |
KR102529631B1 (en) * | 2015-11-30 | 2023-05-04 | 삼성전자주식회사 | Organic photoelectronic device and image sensor |
KR102601600B1 (en) * | 2015-12-24 | 2023-11-14 | 삼성전자주식회사 | Condensed cyclic compound and organic light emitting device including the same |
CN108779072B (en) * | 2016-03-14 | 2021-12-14 | 株式会社Lg化学 | Heterocyclic compound and organic light-emitting element comprising same |
CN106496198A (en) * | 2016-08-31 | 2017-03-15 | 江苏三月光电科技有限公司 | A kind of organic compound and its application with pyridine as core |
CN108203403A (en) * | 2016-12-20 | 2018-06-26 | 武汉尚赛光电科技有限公司 | Luminescent material with thermotropic delayed fluorescence, its application and electroluminescent device |
CN107586299A (en) * | 2017-09-29 | 2018-01-16 | 江苏三月光电科技有限公司 | A kind of organic compound and its application using pyridine as core |
CN109879796A (en) * | 2019-04-13 | 2019-06-14 | 硕明(常州)光源科技有限公司 | A kind of preparation method and applications of organic photoelectrical material |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5942340A (en) * | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
US5952115A (en) * | 1997-10-02 | 1999-09-14 | Xerox Corporation | Electroluminescent devices |
JP4707082B2 (en) * | 2002-11-26 | 2011-06-22 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
KR100695106B1 (en) * | 2002-12-24 | 2007-03-14 | 삼성에스디아이 주식회사 | Blue electroluminescent polymer and organo-electroluminescent device employing the same |
KR101030010B1 (en) * | 2004-09-18 | 2011-04-20 | 삼성모바일디스플레이주식회사 | Blue electroluminescent polymer and organoelectroluminescent device employing the same |
DE102005023437A1 (en) * | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Connections for organic electronic devices |
US7993760B2 (en) * | 2005-12-01 | 2011-08-09 | Nippon Steel Chemical Co., Ltd. | Compound for use in organic electroluminescent device and organic electroluminescent device |
DE102006031990A1 (en) * | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | New materials for organic electroluminescent devices |
KR20080047209A (en) | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | Organic light emitting compound and organic light emitting device comprising the same |
CN101641337A (en) * | 2007-03-27 | 2010-02-03 | 新日铁化学株式会社 | Compound for organic electroluminescent device and organic electroluminescent device |
TWI468489B (en) * | 2007-05-29 | 2015-01-11 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent element compounds and organic electroluminescent elements |
WO2008146838A1 (en) * | 2007-05-30 | 2008-12-04 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display device and illuminating device |
KR20090024998A (en) * | 2007-09-05 | 2009-03-10 | 제일모직주식회사 | Material for organic photoelectric device comprising electron transporting unit and hole transporting unit, and organic photoelectric device thereby |
DE102009023155A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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